The 10 Greatest Investments These Billionaire and Millionaire Entrepreneurs Made

Take the time to build your greatest assets.

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Money, time, vision, sacrifice: investment takes many forms for entrepreneurs. Here's how 10 millionaire (and billionaire) members of The Oracles did it right.

Gary Vaynerchuk
Image Credit: The Oracles

1. Branding.

If you can afford to, invest in branding. Think of branding as getting married and selling as hooking up. It's why I'm winning; I'm branding while everyone is selling. Even the little things I sell—like shirts or a $13 book every three years—is branding. I don't care about the money; my economics just reinforce long-term branding and awareness. The quickest way I know somebody doesn't think they're big time is by their short-term behavior. Gary Vaynerchuk, founder and CEO of VaynerMedia (700+ employees with more than $100 million in annual revenue) and the NYT-bestselling author of "#AskGaryVee"

Tim Draper
Image Credit: The Oracles

2. Investing in tech.

Hotmail was a turning point for me. I came up with the idea for viral marketing so that Hotmail could be spread from customer to customer like a virus. All of a sudden, one of the companies I'd seeded was a household name. It made fundraising easier, and more entrepreneurs wanted my backing and advice. Hotmail affected an extraordinary number of people: approximately 3 billion people communicate through the internet for free, largely due to Hotmail. Tim Draper, founding partner of VC firm DFJ

Barbara Corcoran
Image Credit: The Oracles

3. Seeding passionate entrepreneurs.

The fastest money I ever made was investing in a young technology startup before I sold my brokerage business. I didn't even understand what the guy actually did, but he was hard up for money, and I believed he would find a way to succeed. I bought 10 percent of his business for $100,000 and forgot about it until he bought it back from me for $1 million five years later. I used that million dollars to invest in my first 15 businesses on "Shark Tank." Barbara Corcoran, founder of The Corcoran Group and Shark on "Shark Tank"

Tom Ferry
Image Credit: The Oracles

4. Hiring a legend.

I invested in my exposure by hiring the legendary consultant and creative thinker, Mike Vance. At a pivotal time in my career, I'd achieved several significant milestones but knew my potential was greater. I'd gone as far as I could go alone. I needed a different type of out-of-the-box thinking to break through. So, I hired Mike—not easy to do—and I convinced him to meet me in Miami for a day. I flew in the night before, carefully charting my progress over the last decade, and prepared 22 questions for his guidance. When we met, it was magical. He was the first Dean of Disney University, and had worked with Walt Disney, Jack Welch at GE, Steve Jobs at Apple, and countless other historical business figures. My first question was: "What did they all have in common?" —Tom Ferry, founder and CEO of Tom Ferry International, ranked the number-one real estate coach by the Swanepoel Power 200, and NYT-bestselling author of "Life! By Design"

Roberto Orci
Image Credit: The Oracles

5. Earning team loyalty.

In Hollywood, they say that you should never invest your own money in a project. And I agree with that advice, but during the years that I've had a production company financed by a studio, I've invested in my employees above and beyond what the studios would pay: this has meant giving bonuses, Christmas parties, longer vacation, and most of all, my time. The loyalty I have been rewarded with has been worth the price. Invest in your people and they will invest in you. Roberto Orci, Hollywood super producer and screenwriter whose movies and TV shows have grossed over $5 billion worldwide

James Swanwick
Image Credit: The Oracles

6. Pay to get rich.

At 37, I quit my dream job as an ESPN SportsCenter anchor and was struggling as an entrepreneur, making less than $40,000 a year. So, I invested $25,000 in one-to-one coaching with investor Tai Lopez. I'd previously gotten free coaching, but didn't value it. Investing a huge amount of money to be coached by someone 10 years ahead of me made me focus, show up, and listen. I had skin in the gamefailing to take action would mean setting fire to my money. Coaching accelerated my learning, prevented costly mistakes, and held me accountable. It propelled me to build a seven-figure business, write a book, and launch a podcast. Whenever I want something done, I pay for it. James Swanwick, entrepreneur, author, and CEO of Swanwick Sleep and the 30-Day No Alcohol Challenge

Jon Braddock
Image Credit: The Oracles

7. Investing in me ...

Continually investing in myself has dramatically improved my business and life. I look for ways to educate and improve myself by gathering knowledge and connections to keep moving forward. For the last 20 years, I've invested in groups like Strategic Coach to develop as an entrepreneur, and mastermind groups to connect with amazing individuals who advise and guide me. Remember: knowledge and information are powerfulyou make wiser decisions, identify better opportunities, and gain insights to avoid bad business dealings. Jon Braddock, founder and CEO of My Life & Wishes

8. … myself ...

My greatest investment has been in myself—to know who I am, my identity and purpose. Some call it "mindset," but I prefer "reset." I focus on personal development, reading, and yoga—for example, attending a 10-day silent meditation Vipassana course. Making money is the simplest thing in the world; keeping it is another issue. As a multi-millionaire, I've learned that the moment you put meaning to your ambitions—with service, contribution, and gratitude—is the moment life attracts everything you want. Roy McDonald, founder and CEO of OneLife

Jay Georgi
Image Credit: The Oracles

9. … and I.

I voraciously read, watch biographies, and study disruptive business models. I spent enormous amounts of time away from my wife and kids working on bettering myself, going to work early, coming home late, and then grabbing a book. I've learned there's no such thing as a work-life balance: it's what you make of it. If I stop learning, I become irrelevant and can no longer contribute. To succeed, be radically different from the masses; otherwise, you're copycatting someone's business model, hoping for their success to become yours. Success can only be defined by you: If you want to be in the top one percent, are you willing to pay the price? Are you willing to sacrifice and push through the discouragements? —Jay Georgi, founder of Nadvia and operations / management / profits-retention coach

Phil Suslow
Image Credit: The Oracles

10. Globetrotting.

Unique travel experiences are my greatest investment. Physical possessions come and go, but I'll always cherish the time I spent sailing around Antarctica for two months, skydiving over glaciers in New Zealand, riding horses across Mongolia, or gorilla tracking in Uganda. I recently celebrated with a friend who's visited every country in the world. In my mind, he's way more "wealthy" and interesting than a billionaire who's only been to 10 countries. Travel teaches us about the world, but more importantly, we come back from each trip with a clearer view of ourselves. — Phil Suslow, owner of Oznium

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